Oakland Vacations from $729
Book a Hotel + Flight or Car together to unlock savings
Your Oakland Vacation
From its cycling to its walking, there's tons to love about Oakland. Book a customized Oakland vacation package and get ready to fall for the delights of this neighborhood. When it's time to head out and explore, you'll find lots of big-name attractions nearby including Acrisure Stadium, University of Pittsburgh and PNC Park. Tick off one, two or all during your trip to Oakland. No matter your travel plans or budget, booking the ultimate Oakland vacation is simple with Expedia.
The Latest Oakland Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Oakmont Inn
Plum
Price was $1,104, price is now $926 per person
$926
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Pittsburgh (PIT)
10/10 Exceptional! (37 reviews)
From the minute we arrived to the minute we checked out, an amazing stay, very clean, beds comfortable, convenient location. Great space downstairs for family, gym, and breakfast each morning was wonderful. Will stay here again and recommend to friends and family
Reviewed on Jul 5, 2026
Etage Executive Living
Downtown Pittsburgh
Price was $998, price is now $853 per person
$853
per person
Oct 9 - Oct 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
9.2/10 Wonderful! (1,805 reviews)
The room was dirty, fridge was filthy, pillow and bedding had bloodstains on them. We had planned to stay 4 nights and only ended up staying one. Couldn’t stand being in there especially for the price paid.
Reviewed on Jul 21, 2026
Where to stay in Oakland
Find the best Oakland areas and neighborhoods for the activities you enjoy most. Learn more about Oakland
Downtown Pittsburgh
2 out of top 10 points of interest in this area
Discover the urban downtown center, home to historic sites like Point State Park and the Cultural District. Enjoy diverse shopping options and easy access to public transportation, including the "T" light rail and bus networks.
Oakland Hotel Deals
Courtyard by Marriott Pittsburgh University Center
100 Lytton Avenue Pittsburgh PA
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $158 total per night from Aug 2 to Aug 3
$158 total
Aug 2 - Aug 3
Total with taxes and fees
9/10 Wonderful! (813 reviews)
"Beautiful hotel, clean room, friendly staff, swimming pool was great!"
Reviewed on Jul 20, 2026
Hotel Indigo Pittsburgh University-Oakland by IHG
329 Technology Drive Pittsburgh PA
Fully refundable
$103 nightly
The price is $117 total per night from Aug 2 to Aug 3
$117 total
Aug 2 - Aug 3
Total with taxes and fees
The Oaklander Hotel, Autograph Collection
5130 Bigelow Boulevard Pittsburgh PA
Fully refundableReserve now, pay when you stay
$212 nightly
The price is $242 total per night from Aug 2 to Aug 3
$242 total
Aug 2 - Aug 3
Total with taxes and fees
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Stay near popular Oakland attractions
Things to do
Pittsburgh Pirates Baseball Game at PNC Park
$47
per adult
100% of travellers recommend
Pittsburgh: Museum of Illusions Entrance Ticket
$29
per adult
90% of travellers recommend
Black & Gold Pittsburgh History Tour for Sports Fans
$33
per adult
Explore a world of travel with Expedia
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- Visit Downtown Pittsburgh
- Schenley Park
- Carnegie Museum of Art
- Strip District Vacations
- Cathedral of Learning
- Pittsburgh Vacations
- Carnegie Mellon University
- North Shore Vacations
- National Aviary
- Acrisure Stadium
- Carnegie Library of Pittsburgh
- Byham Theater
- Carnegie Science Center
- Grandview Overlook
- Andy Warhol Bridge
- Children's Museum of Pittsburgh
- Monongahela Incline
- Senator John Heinz Regional History Centre
- Lighthouse ArtSpace Pittsburgh
- Visit Pittsburgh
- Duquesne Incline
- University of Pittsburgh
- Phipps Conservatory
- Ppg Paints Arena
- Kennywood
- Where to stay in Pittsburgh
- Roberto Clemente Bridge
- Andy Warhol Museum
- Petersen Events Center
- Point State Park
- The Nationality Rooms
- David L Lawrence Convention Center
- U.s. Steel Tower
- Heinz Memorial Chapel
- Soldiers and Sailors Memorial Hall and Museum
- Market Square
- Pnc Park
- Photo Antiquities Museum of Photographic History
- Carnegie Museum of Natural History
- Rachel Carson Bridge
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.